Hydrazine → 6-Bromophthalazin-1(2h)-one
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=O)[O:6][CH:5]2O.[NH2:13][NH2:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:6])[NH:14][N:13]=[CH:5]2Participants
Procedure
5-Bromo-3-hydroxyphthalide is reacted in alcoholic solution with hydrazine to give 6-bromophthalazin-1(2H)-one which in turn is reacted with the appropriate (dialkylamino)alkylhalide in a polar solvent such as DMSO in the presence of a base such as KOH to give the 2-(dialkylaminoalkyl)-6-bromophthalazin-1(2H)-one. The styryl group is then attached by reacting the 6-bromo-2-substituted-phthalazin-1(2H)-one with styrene or 4-methoxystyrene in solvents such as DMSO or acetonitrile or mixtures thereof, in the presence of the reagents tri(o-tolyl)phosphine and palladium acetate to give the 6-[2-(phenyl or 4-methoxyphenyl)ethenyl]-2-[(dialkylamino)-alkyl]phthalazin-1(2H)-one. Specific methods for preparing the compounds of this invention are disclosed in the examples.
Sources & evidence
- ORD record
- ord-2307b428fcdc4c0d95e6c98e484f3c9a
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04769369
Reaction notes
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